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to who vs who to?

I couldn't explain to my student when he asked me why 1 doesn't work, while 2 works. When a preposition comes before who, it doesn't work, while the latter works. I told him it's just idiomatic, inexplicable, but do I need to explain this? Can you explain why?

ex1) I met the boy towho I gave the book.(x)
ex2) I met the boy who I gave the book to.(0)

Re: to who vs who to?

Originally Posted by 5jj

If you are going to put 'to' before the relative, it needs to be 'to whom'.

I know it, but they are curious why "to whom" works, while "to who" doesn't. There's no reason like why human beings have brains. Right?
Okay, a second thought tells me "whom" is objective, while "who" is subjective, but what confuses learners is that "who.......to" works.

Re: to who vs who to?

Originally Posted by keannu

I know it, but they are curious why "to whom" works, while "to who" doesn't. There's no reason like why human beings have brains. Right?

It's quite simple. For most users of BrE, 'whom' is dead. Also, most speakers of BrE naturally and happily send the preposition to the end; 'to who(m)' is used only rather formally; people who speak formally tend to use use 'whom' when it is appropriate.

On your second point, most speakers of BrE do not give a thought to whether 'who' functions as a subject, direct object or prepositional object.